There were once high hopes for the 24-year-old first baseman, as he skyrocketed through Boston’s farm system, reaching Double-A in his age-20 season. After that, however, came a free fall of regression, featuring mediocre performances at both Double- and Triple-A, and blown opportunities during three separate cups of coffee with the Red Sox.

Selected by the Red Sox in the 18th-round of the 2006 draft, most teams passed on Anderson due to concerns over his signability. However, Boston inked him for $825k—well above the suggested slot bonus.

A 6’4”, 215-pound left-handed hitter, Anderson enjoyed his best season in 2008 when he batted .317/.417/.517 with 51 extra-base hits and 107 K/75 BB between High- and Double-A.

Anderson’s impressive 2008 campaign led to his ranking as the Red Sox No. 1 prospect and No. 19 overall prospect headed into the 2009 season, according to Baseball America.

Spending the entire season at Double-A, Anderson’s stock took a major hit when he batted .233/.328/.345 in 119 games. Failing to hit double-digit home runs for the first time in his minor league career, the slugger also posted a disconcerting 114 K/63 BB, exposing a hole in both his swing and approach.

He began the 2010 season at Double-A, again, and after a hot start was promoted to Triple-A. Although his power numbers stabilized, Anderson’s swing-and-miss tendency intensified as he recorded 125 K/51 BB.

However, he did receive a September call-up with Red Sox, appearing in 18 games and posting a .554 OPS in 43 plate appearances.

As expected, Anderson didn’t impress enough in his cup of coffee for a crack at first base, and once again spent the season at Triple-A.

And, once again, after another season of mediocrity, he received a cup of coffee in September of 2011. The left-handed hitter was hitless in five at-bats while appearing in six games.

Although he didn’t break camp with the team this season out of spring training, Anderson was recalled for a week towards the end of April. Playing in six games, he recorded one hit in eight at-bats before a demotion back to Triple-A.

Over the last three seasons, there have been countless opportunities to incorporate Anderson’s left-handed bat into the lineup. Therefore, the fact the Red Sox seemingly explored every possible alternative conveyed a strong lack of trust—he didn’t fit into their long-term agenda.

Despite Anderson’s impressive on-base skills, his power has vanished in recent years. Given his status as a first-base prospect, his below-average power (relative to the position) simply doesn’t profile in the major leagues. The power is definitely still there, it’s just a matter of squaring up the baseball with greater consistency.

The Red Sox clearly identified the concerns with Anderson’s offensive ceiling years ago, so it’s somewhat surprising that he hasn’t already been moved.

But it’s not like the Red Sox haven’t tried.

Anderson’s name was in the mix during discussions to potentially acquire Roy Halladay in 2009. He was almost dealt for Rich Harden around this time last year and was mentioned as part of a deal to land Andrew Bailey this past offseason.

His contact rates may never improve and there’s a strong chance he’ll never tap into the robust power, but for a player who was considered one of the game’s top prospects just a few years ago, perhaps a change of scenery is just what he needs.